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Compound Detail

CHEMBL383541

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N[C@H](COc1cncc(/C=C/c2ccncc2)c1)Cc1c[nH]c2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL383541
Phase Preclinical
Structure Type MOL
InChI Key SGHXFHRRWFLILP-XJDXJNMNSA-N
9
Targets
21
Activities
2
Assay Types
16
PK Parameters
20
Publications
0
Known Names

Molecular Properties

370.5
MW (Da)
4.08
ALogP
4
HBA
2
HBD
76.8
PSA (Ų)
0.51
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C23H22N4O
MW 370.46
Aromatic Rings 4
Heavy Atoms 28
NP-Likeness -0.46

Activity Summary

IC50 19 meas. best 7.85
EC50 2 meas. best 5.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
RAC-alpha serine/threonine-protein kinase
CHEMBL4282
 IC50 7.85 6.636 14.0 5
cAMP-dependent protein kinase (PKA)
CHEMBL2094138
 IC50 7.42 7.42 38.0 2
RAC-beta serine/threonine-protein kinase
CHEMBL2431
 IC50 6.59 6.59 257.0 2
RAC-gamma serine/threonine-protein kinase
CHEMBL4816
 IC50 6.45 6.45 354.0 2
Protein kinase C delta type
CHEMBL2996
 IC50 6.03 6.03 930.0 1
Protein kinase C gamma type
CHEMBL2938
 IC50 5.92 5.92 1200.0 1
RAC-alpha serine/threonine-protein kinase
CHEMBL4282
 EC50 5.0 5.0 10000.0 2
MIA PaCa-2
CHEMBL614725
 IC50 4.92 4.92 12000.0 2
Mitogen-activated protein kinase 1
CHEMBL4040
 IC50 4.89 4.89 12850.0 2
Serine/threonine-protein kinase Chk1
CHEMBL4630
 IC50 4.8 4.8 16000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 20.0 mL.min-1.kg-1 Rattus norvegicus
CL 95.0 mL.min-1.kg-1 Mus musculus
CL 41.67 mL.min-1.kg-1 Canis lupus familiaris
CL 26.67 mL.min-1.kg-1 Macaca mulatta
Cmax 809.8 nM Rattus norvegicus
Cmax 7504.18 nM Mus musculus
Cmax 269.93 nM Canis lupus familiaris
Cmax 107.97 nM Macaca mulatta
F 21.0 % Rattus norvegicus
F 39.0 % Mus musculus
F 52.0 % Canis lupus familiaris
F 12.0 % Macaca mulatta
T1/2 3.1 hr Rattus norvegicus
T1/2 0.8 hr Mus musculus
T1/2 3.2 hr Canis lupus familiaris
T1/2 3.7 hr Macaca mulatta

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
RAC-alpha serine/threonine-protein kinase IC50 = 14.0 nM 7.85 Inhibition of Akt1 using 10 uM ATP 16403626
RAC-alpha serine/threonine-protein kinase IC50 = 14.0 nM 7.85 Inhibition of Akt1 at 10 uM ATP 16413780
cAMP-dependent protein kinase (PKA) IC50 = 38.0 nM 7.42 Inhibition of PKA using 10 uM ATP 16403626
cAMP-dependent protein kinase (PKA) IC50 = 38.0 nM 7.42 Inhibition of PKA at 10 uM ATP 16413780
RAC-beta serine/threonine-protein kinase IC50 = 257.0 nM 6.59 Inhibition of Akt2 using 10 uM ATP 16403626
RAC-beta serine/threonine-protein kinase IC50 = 257.0 nM 6.59 Inhibition of Akt2 at 10 uM ATP 16413780
RAC-gamma serine/threonine-protein kinase IC50 = 354.0 nM 6.45 Inhibition of Akt3 using 10 uM ATP 16403626
RAC-gamma serine/threonine-protein kinase IC50 = 354.0 nM 6.45 Inhibition of Akt3 at 10 uM ATP 16413780
RAC-alpha serine/threonine-protein kinase IC50 = 360.0 nM 6.44 Inhibition of Akt 19497644
Protein kinase C delta type IC50 = 930.0 nM 6.03 Inhibition of PKCdelta at 10 uM ATP 16413780
Protein kinase C gamma type IC50 = 1200.0 nM 5.92 Inhibition of PKCgamma at 10 uM ATP 16413780
RAC-alpha serine/threonine-protein kinase IC50 = 3000.0 nM 5.52 Antiproliferative activity against Akt1 overexpressing murine FL5.12-Akt1 cell 16413780
RAC-alpha serine/threonine-protein kinase IC50 = 3000.0 nM 5.52 Antiproliferative activity against FL5.12-Akt1 cells by MTT assay 16403626
RAC-alpha serine/threonine-protein kinase EC50 = 10000.0 nM 5.0 Activity against GSK3 phosphorylation in FL5.12-Akt1 cells 16413780
RAC-alpha serine/threonine-protein kinase EC50 = 10000.0 nM 5.0 Activity against GSK3 in FL5.12-Akt1 cells 16403626
MIA PaCa-2 IC50 = 12000.0 nM 4.92 Antiproliferative activity against MiaPaCa-2 cells by MTT assay 16403626
MIA PaCa-2 IC50 = 12000.0 nM 4.92 Antiproliferative activity against human MiaPaCa-2 cells 16413780
Mitogen-activated protein kinase 1 IC50 = 12850.0 nM 4.89 Inhibition of ERK2 using 10 uM ATP 16403626
Mitogen-activated protein kinase 1 IC50 = 12850.0 nM 4.89 Inhibition of ERK2 at 10 uM ATP 16413780
Serine/threonine-protein kinase Chk1 IC50 = 16000.0 nM 4.8 Inhibition of Chk1 using 10 uM ATP 16403626

Literature References

PubMed DOI Target Context # Activities
16403626 10.1016/j.bmcl.2005.12.017 Rhesus monkey 5
16403626 10.1016/j.bmcl.2005.12.017 Canis familiaris 5
16403626 10.1016/j.bmcl.2005.12.017 Mus musculus 5
16403626 10.1016/j.bmcl.2005.12.017 Rattus norvegicus 5
16403626 10.1016/j.bmcl.2005.12.017 RAC-alpha serine/threonine-protein kinase 3
16413780 10.1016/j.bmcl.2005.12.065 RAC-alpha serine/threonine-protein kinase 3
19497644 10.1016/j.ejmech.2009.04.050 RAC-alpha serine/threonine-protein kinase 1
16403626 10.1016/j.bmcl.2005.12.017 RAC-beta serine/threonine-protein kinase 1
16413780 10.1016/j.bmcl.2005.12.065 cAMP-dependent protein kinase (PKA) 1
16413780 10.1016/j.bmcl.2005.12.065 RAC-gamma serine/threonine-protein kinase 1
16413780 10.1016/j.bmcl.2005.12.065 RAC-beta serine/threonine-protein kinase 1
16403626 10.1016/j.bmcl.2005.12.017 MIA PaCa-2 1
16403626 10.1016/j.bmcl.2005.12.017 Proto-oncogene tyrosine-protein kinase Src 1
16403626 10.1016/j.bmcl.2005.12.017 Mast/stem cell growth factor receptor Kit 1
16403626 10.1016/j.bmcl.2005.12.017 Vascular endothelial growth factor receptor 3 1
16403626 10.1016/j.bmcl.2005.12.017 Vascular endothelial growth factor receptor 2 1
16403626 10.1016/j.bmcl.2005.12.017 Serine/threonine-protein kinase Chk1 1
16403626 10.1016/j.bmcl.2005.12.017 Casein kinase II 1
16403626 10.1016/j.bmcl.2005.12.017 Mitogen-activated protein kinase 1 1
16403626 10.1016/j.bmcl.2005.12.017 cAMP-dependent protein kinase (PKA) 1

Data from ChEMBL 36 via Core Engine